* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With Aliquat(at)366; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24 h;
General procedure: A mixture of p-fluorobenzaldehyde 1 (25.0 g, 0.200 mol) andappropriate amine 2a–g (0.300 mol) and anhydrous potassium carbonate(40.0 g) were mixed in DMF (300mL), after which catalyticamount of Aliquat 336 reagent was added. The mixture was thenrefluxed for 24 h at 100 C. The mixture was concentrated underlow pressure and left to cool. The mixture was then poured into icewater and left overnight. The formed solid was filtered, washed withwater and crystallized with methanol to yield compounds Ia–g. 4-(1H-imidazol-1-yl) benzaldehyde Ia Yield 92percent as yellow crystals, mp 152 °C, (as reported) [34,44].
76%
With potassium carbonate In N,N-dimethyl-formamide at 110℃;
General procedure: A mixture of 4-fluoro acetophenone/4-fluorobenzaldehyde (10 mmol) and imidazole/triazole (10 mmol) were dissolved in dry DMF (20 mL). K2CO3 (12 mmol) was added in small portion within a period of 15 min to the above stirred solution. Mixture was stirred for 10-12 h at 110 °C. Heating discontinued, K2CO3 was filtered off, filtrate extracted with ethyl acetate (3 .x. 15 mL). Organic layer was washed with water (3 .x. 15 mL), dried over anhydrous sodium sulphate and concentrated to given an oil which was purified on silica gel column (60-120 mesh) taking methanol: chloroform (1:99) as an eluent.
1 g
With potassium carbonate In N,N-dimethyl-formamide for 6 h; Reflux
Intermediate 1 Ethyl 5-(4-(lH-imidazol- l-yl)phenyl)-4H-thieno[3,2-^]pyrrole-2-carboxylate Step- 1 : Preparation of 4-(lH-imidazol-l-yl)benzaldehyde To a solution of 4-fluorobenzaldehyde (1.0 g, 8.06 mmol) in DMF (3 mL) were added 1H- imidazole (2.1 g, 32.2 mmol) and K2C03 (2.2 g, 16.12 mmol). The reaction mass was heated at reflux for 6 h before it was diluted with water and was extracted with EtOAc. The organic layer was separated, dried, filtered and concentrated. The residue was purified by column chromatography to afford 1.0 g of the title product. 1H NMR (300 MHz, DMSO d6) δ 10.03 (s, 1H), 8.47 (s, 1H), 8.07-8.04 (d, = 8.4 Hz, 2H), 7.95-7.93 (m, 3H), 7.17 (s, 1H); MS (m/z): 173 (M+H)+.
Reference：
[1] Synthetic Communications, 2008, vol. 38, # 4, p. 626 - 636
[2] New Journal of Chemistry, 2007, vol. 31, # 6, p. 906 - 910
[3] Bioorganic Chemistry, 2014, vol. 57, p. 65 - 82
[4] Journal of Molecular Structure, 2007, vol. 829, # 1-3, p. 202 - 207
[5] Advanced Synthesis and Catalysis, 2007, vol. 349, # 11-12, p. 1938 - 1942
[6] Journal of the American Chemical Society, 2005, vol. 127, # 28, p. 9948 - 9949
[7] European Journal of Medicinal Chemistry, 2009, vol. 44, # 11, p. 4654 - 4660
[8] Medicinal Chemistry Research, 2013, vol. 22, # 11, p. 5248 - 5254
[9] European Journal of Medicinal Chemistry, 2011, vol. 46, # 9, p. 4302 - 4310
[10] Tetrahedron, 2001, vol. 57, # 22, p. 4781 - 4785
[11] Monatshefte fur Chemie, 2004, vol. 135, # 4, p. 419 - 423
[12] Tetrahedron, 2008, vol. 64, # 8, p. 1823 - 1828
[13] Journal of Medicinal Chemistry, 1998, vol. 41, # 13, p. 2390 - 2410
[14] Chemical Communications, 2018, vol. 54, # 69, p. 9603 - 9606
[15] Journal of Medicinal Chemistry, 1987, vol. 30, # 6, p. 1023 - 1029
[16] RSC Advances, 2015, vol. 5, # 92, p. 75425 - 75433
[17] Patent: US7138432, 2006, B1, . Location in patent: Page/Page column 46
[18] Tetrahedron Letters, 2009, vol. 50, # 12, p. 1286 - 1289
[19] Journal of Organic Chemistry, 2013, vol. 78, # 7, p. 3222 - 3234
[20] Medicinal Chemistry Research, 2013, vol. 22, # 4, p. 1756 - 1761
[21] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 7, p. 1695 - 1697
[22] Journal of Chemical Research, 2014, vol. 38, # 8, p. 498 - 501
[23] Patent: WO2016/128905, 2016, A1, . Location in patent: Page/Page column 47
[24] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 12, p. 1107 - 1111
[25] Supramolecular Chemistry, 2017, vol. 29, # 3, p. 193 - 204
[26] Medicinal Chemistry Research, 2017, vol. 26, # 7, p. 1506 - 1515
[27] Molecules, 2017, vol. 22, # 8,
[28] Patent: CN104130192, 2017, B, . Location in patent: Paragraph 0033-0034
[29] Patent: CN107043353, 2017, A, . Location in patent: Paragraph 0034
2
[ 288-32-4 ]
[ 15164-44-0 ]
[ 10040-98-9 ]
Yield
Reaction Conditions
Operation in experiment
94%
With potassium carbonate In dimethyl sulfoxide at 120℃; for 12 h; Inert atmosphere
General procedure: To a mixture of 0.05 g catalyst and aryl halide (1.0 mmol)in 9.0 cm3 DMSO, Het-NH (1.2 mmol) and K2CO3(2.0 mmol) was added and the mixture was vigorouslystirred at 120 C for the appropriate time under a drynitrogen atmosphere. After completion (as monitored byTLC), the catalyst was filtered, and the filtrate wasextracted with ethyl acetate (3 9 20 cm3) and the combinedorganic layers were dried with anhydrous MgSO4,filtered, and evaporated under reduced pressure. The residuewas purified by column chromatography. The purity ofthe compounds was checked by 1H NMR and yields arebased on aryl bromide. All the products are known and thespectroscopic data (FT-IR and NMR) and melting pointswere consistent with those reported in the literature [36–41].
93%
With copper(l) chloride; sodium hydroxide; 3-(diphenylphosphino)propionic acid In dimethyl sulfoxide at 120℃; for 14 h; Inert atmosphere; Sealed tube
General procedure: NH-containing heterocycle (1.4 mmol) and DMF (2.0 mL) were added to a mixture of CuCl (15.0 molpercent) and ligand 1 (20.0 molpercent) in DMF (2.0 mL), aryl iodide (1.0 mmol), NaOH (2.0 mmol). The mixture was vigorously stirred at 120 °C for 14 h under a dry nitrogen atmosphere. After completion of the reaction (as monitored by TLC), H2O was added and the organic layer was extracted with EtOAc, washed with brine and dried over MgSO4. The solution was filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography. The purity of the compounds was checked by 1H NMR and yields are based on aryl iodide. All the products are known and the spectroscopic data (FT‑IR and NMR) and melting points were consistent with those reported in the literature.
90 %Chromat.
With C16H12ClN3OPdS; potassium hydroxide In dimethyl sulfoxide at 110℃; for 10 h;
General procedure: Arylhalide (1.0 mM), nitrogen-containing heterocycle (1.2 mM), KOH (2 mM), and the catalyst (0.75 Mpercent) were stirred in dimethyl sulfoxide (DMSO) (4 mL) at 110 °C for 10 h. After completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate (10 mL) and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel using hexane/ethyl acetate(70 : 30) as eluent to afford the desired product. The products have been characterized by 1H NMR spectroscopy.
Reference：
[1] Journal of Organic Chemistry, 2009, vol. 74, # 5, p. 2200 - 2202
[2] Monatshefte fuer Chemie, 2015, vol. 146, # 8, p. 1329 - 1334
[3] Journal of Chemical Research, 2014, vol. 38, # 2, p. 128 - 129
[4] Journal of Coordination Chemistry, 2015, vol. 68, # 19, p. 3537 - 3550
3
[ 288-32-4 ]
[ 1122-91-4 ]
[ 10040-98-9 ]
Yield
Reaction Conditions
Operation in experiment
67%
With potassium carbonate In N,N-dimethyl-formamide at 152℃; for 26 h;
General procedure: To a vigorously stirred suspension of the CuNPs/MagSilica catalyst (100 mg) in DMF (6 mL) under air, K2CO3 (276 mg, 2.0 mmol) and imidazole (136 mg, 2.0 mmol) were added. The reaction mixture was stirred for 30 min and then the corresponding aryl halide (1.0 mmol) was added and the reaction flask was immersed in an oil bath at the reflux temperature of DMF (152 °C). The reaction mixture was stirred at this temperature until no further conversion of the starting aryl halide was observed (TLC, GC). The catalyst was immobilized by means of a permanent magnet placed on the outer wall of the reaction flask, and washed twice with Et2O (10 mL each). Finally, the catalyst was dried under vacuum (5 Torr) for its recovery and reuse. The crude reaction mixture was evaporated under vacuum (15 Torr) and the resulting residue was purified by flash column chromatography (silica gel, hexane/AcOEt) to afford the corresponding N-aryl imidazoles (2a-j). All known compounds included in Table 1 were characterized by comparison of their chromatographic and spectroscopic data (1H, 13C NMR, and MS) either with those of the corresponding commercially available pure samples (2g) or with those described in the literature (2a,21 2b,212c,22 2d,21 2e,11a 2f,11a 2h,23 2i,24 2j25).
85 %Chromat.
With C16H12ClN3OPdS; potassium hydroxide In dimethyl sulfoxide at 110℃; for 10 h;
General procedure: Arylhalide (1.0 mM), nitrogen-containing heterocycle (1.2 mM), KOH (2 mM), and the catalyst (0.75 Mpercent) were stirred in dimethyl sulfoxide (DMSO) (4 mL) at 110 °C for 10 h. After completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate (10 mL) and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel using hexane/ethyl acetate(70 : 30) as eluent to afford the desired product. The products have been characterized by 1H NMR spectroscopy.
Reference：
[1] Tetrahedron, 2008, vol. 64, # 19, p. 4254 - 4259
[2] Tetrahedron, 2008, vol. 64, # 10, p. 2471 - 2479
[3] Tetrahedron Letters, 2006, vol. 47, # 23, p. 3897 - 3899
[4] Synthetic Communications, 2012, vol. 42, # 1, p. 114 - 121
[5] Chinese Journal of Chemistry, 2012, vol. 30, # 10, p. 2394 - 2400
[6] RSC Advances, 2015, vol. 5, # 12, p. 8571 - 8578
[7] Synthetic Communications, 2012, vol. 42, # 2, p. 279 - 284
[8] Research on Chemical Intermediates, 2016, vol. 42, # 10, p. 7501 - 7511
[9] Bulletin of the Chemical Society of Japan, 2008, vol. 81, # 4, p. 515 - 517
[10] Tetrahedron, 2014, vol. 70, # 36, p. 6082 - 6087
[11] Applied Organometallic Chemistry, 2017, vol. 31, # 11,
[12] Inorganic Chemistry, 2010, vol. 49, # 1, p. 331 - 338
[13] Tetrahedron, 2008, vol. 64, # 7, p. 1383 - 1387
[14] European Journal of Medicinal Chemistry, 2009, vol. 44, # 11, p. 4654 - 4660
[15] Journal of Coordination Chemistry, 2015, vol. 68, # 19, p. 3537 - 3550
4
[ 288-32-4 ]
[ 104-88-1 ]
[ 10040-98-9 ]
Reference：
[1] RSC Advances, 2015, vol. 5, # 12, p. 8571 - 8578
[2] Synthetic Communications, 2008, vol. 38, # 4, p. 626 - 636
[3] Journal of Organic Chemistry, 2009, vol. 74, # 20, p. 7951 - 7954
[4] Chemical Communications, 2004, # 7, p. 778 - 779
[5] Advanced Synthesis and Catalysis, 2007, vol. 349, # 11-12, p. 1938 - 1942
[6] Journal of the American Chemical Society, 2005, vol. 127, # 28, p. 9948 - 9949
[7] Tetrahedron, 2008, vol. 64, # 10, p. 2471 - 2479
[8] European Journal of Medicinal Chemistry, 2009, vol. 44, # 11, p. 4654 - 4660
Reference：
[1] European Journal of Medicinal Chemistry, 1992, vol. 27, # 3, p. 219 - 228
12
[ 86718-07-2 ]
[ 10040-98-9 ]
Reference：
[1] European Journal of Medicinal Chemistry, 1992, vol. 27, # 3, p. 219 - 228
13
[ 10602-01-4 ]
[ 10040-98-9 ]
Reference：
[1] Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2964 - 2972
14
[ 67-56-1 ]
[ 10040-98-9 ]
[ 101184-08-1 ]
Yield
Reaction Conditions
Operation in experiment
90%
Stage #1: for 0.25 h; Green chemistry Stage #2: With tert.-butylhydroperoxide In decane for 24 h; Green chemistry
General procedure: B(C6F5)3 (1 mol percent) was added to a stirringsolution of aldehyde (1 mmol) in MeOH (6 mL). After 15 min., 5.5 M TBHP indecane (3 mmol) was added slowly and reaction mixture was refluxed untilthe complete conversion of starting material (monitored by TLC). Aftercompletion of reaction, the methanol was evaporated in vacuo. Later, thereaction mixture was diluted with water (20 mL) and extracted with ethylacetate (3 15 mL). The organic layer was washed with cold saturated sodiumbicarbonate solution (2 20 mL) followed by brine. The organic layer wasdried over MgSO4 and concentrated under reduced pressure and products werepurified over silica gel column chromatography in ethyl acetate/hexane. Allcompounds were characterized and confirmed by comparison of their spectraldata and physical properties with reported literature.
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 1.5h;
92%
With tri-n-octylmethylammonium chloride; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h;
92%
With aliquat 336; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h;
1 General method for preparation of 4-(substituted) benzaldehyde
General procedure: A mixture of p-fluorobenzaldehyde 1 (25.0 g, 0.200 mol) andappropriate amine 2a-g (0.300 mol) and anhydrous potassium carbonate(40.0 g) were mixed in DMF (300mL), after which catalyticamount of Aliquat 336 reagent was added. The mixture was thenrefluxed for 24 h at 100 C. The mixture was concentrated underlow pressure and left to cool. The mixture was then poured into icewater and left overnight. The formed solid was filtered, washed withwater and crystallized with methanol to yield compounds Ia-g. 4-(1H-imidazol-1-yl) benzaldehyde Ia Yield 92% as yellow crystals, mp 152 °C, (as reported) [34,44].
90%
With tri-n-octylmethylammonium chloride; potassium carbonate at 85℃; for 24h;
85%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 2h;
80%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 1h;
79%
With tri-n-octylmethylammonium chloride; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Schlenk technique; Inert atmosphere;
78.3%
With N-hexadecyl-N,N,N-trimethylammonium bromide; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 18h;
78.3%
With N-hexadecyl-N,N,N-trimethylammonium bromide; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 15h;
76%
With potassium carbonate In N,N-dimethyl-formamide at 110℃;
6.1. General procedure for the synthesis of compounds (1a-b and 15a-b)
General procedure: A mixture of 4-fluoro acetophenone/4-fluorobenzaldehyde (10 mmol) and imidazole/triazole (10 mmol) were dissolved in dry DMF (20 mL). K2CO3 (12 mmol) was added in small portion within a period of 15 min to the above stirred solution. Mixture was stirred for 10-12 h at 110 °C. Heating discontinued, K2CO3 was filtered off, filtrate extracted with ethyl acetate (3 × 15 mL). Organic layer was washed with water (3 × 15 mL), dried over anhydrous sodium sulphate and concentrated to given an oil which was purified on silica gel column (60-120 mesh) taking methanol: chloroform (1:99) as an eluent.
75%
With potassium carbonate In dimethyl sulfoxide for 0.25h; ultrasound;
75%
With potassium carbonate In dimethyl sulfoxide at 140℃; for 0.25h; sonification;
72%
With potassium carbonate In N,N-dimethyl-formamide at 30℃; for 10h; Inert atmosphere; Irradiation;
62%
With potassium carbonate In dimethyl sulfoxide at 150℃; for 1h;
55%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 5h;
54%
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; Schlenk technique;
38.9%
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h;
33%
With potassium carbonate In pyridine for 18h; Heating;
28%
Stage #1: 1H-imidazole With N-hexadecyl-N,N,N-trimethylammonium bromide; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 0.166667h;
Stage #2: para-fluorobenzaldehyde In N,N-dimethyl-formamide for 24h;
With potassium carbonate In N,N-dimethyl-formamide at 20 - 100℃; for 5.5h;
80.1
Stage 80.1: 4-Imidazol-1-yl-benzaldehydeTo a solution of 20 g (161.1 mmol) of p-fluorobenzaldehyde in 300 ml of DMF, 19.8 g (290.8 mmol) of imidazole and 44.5 g (322.24 mmol) of potasium carbonate are step by step added at r.t. After being stirred for 5.5 h at 100° C., the reaction mixture is cooled to r.t., diluted with ice water and then the mixture is extracted with AcOEt and CH2Cl2. The combined extracts are concentrated under reduced pressure to give 4-imidazol-1-yl-benzaldehyde as a pale yellow powder. 1H-NMR (400 MHz, CDCl3): 7.26 (s, 1H), 7.38 (2, 1H), 7.59 (d, 2H, J=8.56 Hz), 7.98 (s, 1H), 8.02 (d, 2H, J=8.56 Hz), 10.05 (s, 1H).
74 %Spectr.
With tripotassium phosphate tribasic at 20 - 120℃; for 0.1h; Microwave irradiation;
With potassium carbonate In N,N-dimethyl-formamide
With N-hexadecyl-N,N,N-trimethylammonium bromide; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 28h;
With potassium carbonate In dimethyl sulfoxide Sonication;
With N-hexadecyl-N,N,N-trimethylammonium bromide; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h;
1 g
With potassium carbonate In N,N-dimethyl-formamide for 6h; Reflux;
1.1 Step- 1 : Preparation of 4-(lH-imidazol-l-yl)benzaldehyde
Intermediate 1 Ethyl 5-(4-(lH-imidazol- l-yl)phenyl)-4H-thieno[3,2-^]pyrrole-2-carboxylate Step- 1 : Preparation of 4-(lH-imidazol-l-yl)benzaldehyde To a solution of 4-fluorobenzaldehyde (1.0 g, 8.06 mmol) in DMF (3 mL) were added 1H- imidazole (2.1 g, 32.2 mmol) and K2C03 (2.2 g, 16.12 mmol). The reaction mass was heated at reflux for 6 h before it was diluted with water and was extracted with EtOAc. The organic layer was separated, dried, filtered and concentrated. The residue was purified by column chromatography to afford 1.0 g of the title product. 1H NMR (300 MHz, DMSO d6) δ 10.03 (s, 1H), 8.47 (s, 1H), 8.07-8.04 (d, = 8.4 Hz, 2H), 7.95-7.93 (m, 3H), 7.17 (s, 1H); MS (m/z): 173 (M+H)+.
With potassium carbonate In N,N-dimethyl-formamide Heating;
With N,N,N,N-tetramethylammonium bromide; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 24h;
With potassium carbonate In dimethyl sulfoxide
With potassium carbonate In N,N-dimethyl-formamide at 300℃; for 36h;
3.2.1. Synthesis of 4-substituted Benzaldehydes 1a-1n
General procedure: A mixture of 4-fluorobenzaldehyde (8.85 mL, 0.1 mol), the corresponding phenol, thiophenol or amine (0.1 mol), and a catalytic quantity of potassium carbonate (K2CO3) was refluxed in DMF (20 mL) for 36 h. After completion of the reaction, the mixture was poured into ice-water (50 mL), and the precipitated product was filtered, washed with deionised water, dried, and recrystallized from EtOH.
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 20h;
1
Weighed 0.680 g (10 mmol) of imidazole,1.240 g (10 mmol) of p-fluorobenzaldehyde and 1.380 g (10 mmol) of anhydrous potassium carbonate were weighed and dissolved in 25 mL of N, N-dimethylformamide and added to a 50 mL four-necked flask equipped with a thermometer and a stirrer The flask. 60 under constant temperature for 20h, cooled to room temperature, poured into 100mL ice water, a yellow solid precipitation, filtration, recrystallization with ethanol, vacuum drying at 50 for 8h, that is, 4 - imidazolyl benzaldehyde.
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 20h;
1
0.680 g (10 mmol) of imidazole was weighed and 1.240 g (10 mmol) of p-fluorobenzaldehyde and 1.380 g (10 mmol) of anhydrous potassium carbonate were weighed and dissolved in 25 mL of N, N-dimethylformamide, Thermometer, stirring device 50mL four-necked flask.60 ° C for 20h, cooled to room temperature, poured into 100mL ice water, a yellow solid precipitated, suction filtered, recrystallized from ethanol, dried at 50 ° C for 8h under vacuum to give 4-imidazolyl benzaldehyde
With potassium carbonate In dimethyl sulfoxide Reflux;
With potassium carbonate In dimethyl sulfoxide Reflux;
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 5h; Inert atmosphere;
[1349] 4-(1H-imidazol-1-yl)benzaldehyde : To a solution of 4-fluorobenzaldehyde (1.0 g, 8.05 mmol, 1 eq) in DMF (10.0 mL) was added K2CO3 (1.66 g, 12.07 mmol, 1.5 eq) and then 1H-imidazole (0.66 g, 9.66 mmol, 1.2 eq) was added. The mixture was stirred at 120°C. for 5 h under N2 atmosphere. TLC (50% EtOAc in hexane) showed the reaction was completed. The reaction was cooled to room temperature and was diluted with EtOAc (150 mL), washed with water (220 mL). The organic layer was dried over anhydrous Na2SO4, concentrated under reduced pressure to get the crude. The crude product was purified by flash column chromatography using 50-60% EtOAc in hexane as an eluent to give 4-(1H-imidazol-1-yl)benzaldehyde. LC-MS (m/z)=173.1[M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.14 (s, 1H), 7.90 (d, J=9.6 Hz, 3H), 8.02 (d, J=8.0 Hz, 2H), 8.43 (s, 1H), 10.00 (s, 1H).
Stage #1: 1H-imidazole; para-fluorobenzaldehyde With potassium carbonate In dimethyl sulfoxide for 1h; Sonication;
Stage #2: In dimethyl sulfoxide at 120℃; for 1.5h;
General procedure for the synthesis of 4-azolyl benzaldehydes
General procedure: Azole substituted benzaldehydes were obtained according to the modified reported procedure [23]. 10 mmol azole derivative (pyrazole, imidazole or 1,2,4-triazole) and 10 mmol 4-fluorobenzaldehyde were sonicated for 1 h in 10 mL DMSO in the presence of 11 mmol anhydrous potassium carbonate. Afterward, the reaction mixture was heated in oil bath (120°C) for 1.5 h. The temperature was then decreased to 60°C and the reaction mixture was poured into ice-water. The precipitated solid was filtered, washed with water and used for the next step without any further purification.
With potassium carbonate In dimethyl sulfoxide at 120℃; for 3h; Sonication;
2.2.1. General procedure for the synthtesis of azole linkedbenzaldehydes
General procedure: 4-Azolyl benzaldehydes were obtained based on the modificationof the method reported in the literature [37]. Equimolaramounts of 4-fluorobenzaldehyde and azole derivate (pyrazole,imidazole or 1,2,4-triazole) were sonicated in DMSO in the presenceof anhydrous K2CO3 for 1 h. At the end of the sonication,the reaction mixture was heated in oil bath at 120 C for 2 h. Then,it was poured into ice-water after the temperature decreased to60 C. Finally, the precipitated solid was directly used for the nextstep after filtration and washing with water.
8.51 g of this acetate are added to a solution of 5.12 g of midazole sodium salt in 100 ml of DMF then 3.63 g of Cu powder are added and the mixture is refluxed for 6 hours, cooled, poured into diluited chloridic acid and crushed ice. The mixture is warmed at 50 C. for 1 hour, cooled, washed with methylene chloride, neutralized with NaHCO3, extracted with methylene chloride, dried and evaporated to dryness to give 2.5 g 4-(1-imidazolyl) benzaldehyde. The ethyl-4-(1-imidazolyl)-benzoate is obtained in good yield reacting the ethyl 4-bromobenzoate with imidazole in radicalic condition using CuBr as catalyst.
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(2-fluoro-phenyl)-acrylamide[ No CAS ]
3-(2-chloro-phenyl)-2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-acrylamide[ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(4-hydroxy-phenyl)-acrylamide[ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(2-iodo-phenyl)-acrylamide[ No CAS ]
3-(3-chloro-2-fluoro-phenyl)-2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-acrylamide[ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-naphthalen-2-yl-acrylamide[ No CAS ]
3-(5-bromo-2-fluoro-phenyl)-2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-acrylamide[ No CAS ]
2-cyano-3-(3,4-dimethoxy-phenyl)-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-acrylamide[ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(1-methyl-1H-indol-3-yl)-acrylamide[ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(4-imidazol-1-yl-phenyl)-acrylamide[ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(2-fluoro-4-iodo-phenyl)-acrylamide[ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(2,4,6-trimethyl-phenyl)-acrylamide[ No CAS ]
2-cyano-3-(2-difluoromethoxy-phenyl)-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-acrylamide[ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(4-hydroxy-3,5-dimethyl-phenyl)-acrylamide[ No CAS ]
3-(2-chloro-6-fluoro-3-methyl-phenyl)-2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-acrylamide[ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(2,3,6-trichloro-phenyl)-acrylamide[ No CAS ]
2-cyano-3-(3-ethoxy-2-hydroxy-phenyl)-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-acrylamide[ No CAS ]
{2-[2-cyano-2-(5-ethyl-[1,3,4]thiadiazol-2-ylcarbamoyl)-vinyl]-phenoxy}-acetic acid[ No CAS ]
2-cyano-3-(3,4-dihydroxy-5-methoxy-phenyl)-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-acrylamide[ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(4-hydroxy-3,5-dimethoxy-phenyl)-acrylamide[ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(2-hydroxy-4,6-dimethoxy-phenyl)-acrylamide[ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(3-p-tolyloxy-phenyl)-acrylamide[ No CAS ]
3-(4-benzyloxy-phenyl)-2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-acrylamide[ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(4-hexyloxy-phenyl)-acrylamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
A 0.25 M stock solution of 2-cyano-N- (5-ethyl- [1, 3, 4] thiadiazol-2- yl)-acetamide was prepared in 1.0 M diisopropylethylamine in DMF. Benzaldehyde and other heterocyclic aldehydes were individually weighed and were dissolved to 0.25 M using a Tecan Genesis workstation. The Tecan was used to dispense 200 muL of template 1 to each reaction vessel then was used to dispense 400 L of aldehyde stock solutions to individual reaction vessels. The reaction vessels were sealed and were heated at 45-50 C, with agitation, for 18 hours. The reaction vessels were then cooled, unsealed, and 50 L of aminopropyl-functionalized silica gel (Aldrich) was dispensed to each reaction vessel. Activated 4 angstrom molecular sieves (powdered, 50 L) were then dispensed to each reaction. Reaction vessels were then sealed and were heated at 45-50 C with agitation for 3 h. Reactions were then unsealed and were filtered to remove solids. B. Sample solutions were dried in vacuo using a Genevac. Samples were dissolved in 500 pL of DMSO and 500 pL of methanol and purity was determined by LC-MS with using a combination of UV254, UV220, and ELSD detection [purity = (UV254+UV220/2)]. The HPLC conditions were: 4.6 mm x 50 mm C18 column, 10-90% acetonitrile gradient over 5 minutes (mobile phases were H20 with 0.05 % TFA and acetonitrile with 0.035 % TFA), with a flow rate of 3.5 ml/min. Samples which were <80% pure were purified using a mass directed LC-MS purification. Purified samples were concentrated in vacuo then were dissolved in DMSO and were reformatted into 96 well microtiter plates. Samples were tested for purity using LC-MS and quantity was estimated by correlating ELSD response to a standard concentration-ELSD response curve. Samples were then concentrated to dryness and were dissolved in DMSO to a final concentration of 10 uM based on ELSD quantitation. C. The following compounds were prepared in the manner described above in Steps A and B using the appropriate aldehyde in place of benzaldehyde: 2-Cyano-3- (3, 4-dimethoxy-phenyl)-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)- acrylamide ; MS (ES): 345 (MH+) ; 3- (4-Benzyloxy-phenyl)-2-cyano-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)- acrylamide ; MS (ES) : 391 (MH+) ; 2-Cyano-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)-3- (4-hydroxy-phenyl)- acrylamide ; MS (ES): 301 (MH+) ; Acetic acid 4- [2-cyano-2- (5-ethyl- [1, 3,4] thiadiazol-2-ylcarbamoyl)-vinyl]- phenyl ester; MS (ES): 343 (MH+); 2-Cyano-3- (2, 4-dichloro-phenyl)-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)- acrylamide ; MS (ES): 353 (MH+) ; 3- (2-Bromo-phenyl)-2-cyano-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)- acrylamide ; MS (ES): 363 (MH+) ; 2-Cyano-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)-3- (2-fluoro-phenyl)- acrylamide ; MS (ES): 303 (MH+) ; 3- (4-tert-Butyl-phenyl)-2-cyano-N- (5-ethyl- [1, 3, 4] thiadiazol-2-yl)- acrylamide ; MS (ES): 341 (MH+) ; 3- (2-Chloro-4-fluoro-phenyl)-2-cyano-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)- acrylamide ; MS (ES): 337 (MH+) ; 2-Cyano-3- (2, 5-dimethyl-phenyl)-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)- acrylamide ; MS (ES): 313 (MH+) ; 2-Cyano-5- (4-methoxy-phenyl)-penta-2, 4-dienoic acid (5-ethyl- [1,3, 4] thiadiazol-2-yl)-amide ; MS (ES): 341 (MH+) ; 2-Cyano-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)-3-(4-hydroxy-3, 5-dimethoxy- phenyl)-acrylamide ; MS (ES): 361 (MH+) ; 2-Cyano-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)-3- (4-hydroxy-3-iodo-5- methoxy-phenyl)-acrylamide ; MS (ES): 457 (MH+) ; 2-Cyano-3- (3, 4-dihydroxy-phenyl)-N- (5-ethyl- [1, 3, 4] thiadiazol-2-yl)- acrylamide ; MS (ES): 317 (MH+) ; 2-Cyano-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)-3- (4-hydroxy-3-methoxy-5- nitro-phenyl)-acrylamide ; MS (ES): 376 (MH+) ; 2-Cyano-N- (5-ethyl- [1, 3,4] thiadiazol-2-yi)-3- (4-hydroxy-3-methoxy-5- nitro-phenyl)-acrylamide ; MS (ES): 376 (MH+) ; 3-(4-Benzyloxy-3,5-dimethyl-phenyl)-2-cyano-N-(5-ethyl- [1,3, 4] thiadiazol-2-yl)-acrylamide ; MS (ES): 419 (MH+) ; 2-Cyano-3- (3, 5-dibromo-2-methoxy-phenyl)-N- (5-ethyl- [1, 3,4] thiadiazol- 2-yl)-acrylamide ; MS (ES) : 471 (MH+) ; 2-Cyano-N- (5-ethyl- [1, 3, 4] thiadiazol-2-yl)-3- (4-hexyloxy-phenyl)- acrylamide ; MS (ES): 385 (MH+) ; Acetic acid 4- [2-cyano-2- (5-ethyl- [1, 3,4] thiadiazol-2-ylcarbamoyl)-vinyl]- 2, 6-dimethoxy-phenyl ester; MS (ES): 403 (MH+) ; 2-Cyano-N- (5-ethyl- [1, 3,4] thiadiazol-2-yi)-3- (4-imidazol-1-yi-phenyl)- acrylamide ; MS (ES): 351 (MH+) ; 2-Cyano-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)-3-(2-trifluoromethyl-phenyl)- acrylamide ; MS (ES): 353 (MH+) ; 3- (2-Chloro-3, 4-dimethoxy-phenyl)-2-cyano-N- (5-ethyl- [1, 3,4] thiadiazol- 2-yl)-acrylamide ; MS (ES): 379 (MH+) ; 2-Cyano-N- (5-ethyl- [1, 3, 4] thiadiazol-2-yl)-3- ( 1-methyl-1 H-indol-3-yl)- acrylamide ; MS (ES): 338 (MH+) ; 2-Cyano-3- (2, 6-dichloro-phenyl)-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)- acrylamide ; MS (ES): 353 (MH+) ; 2-Cyano-3-(4-dimethylamino-2-nitro-phenyl)-N-(5-ethyl-[1, 3,4] thiadiazol- 2-yl)-acrylamide ; MS (ES): 373 (MH+) ; 2-Cyano-N-(5-ethyl-[1, 3,4] thiadiazol-2-yl)-3- (2-iodo-phe...
With hydrogenchloride; n-butyllithium; p-toluenesulfonic acid monohydrate; sodium carbonate In tetrahydrofuran; methanol; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; ice-water; hexane; water; palladium; isopropyl alcohol
19.a EXAMPLE 19
(a) 53.1 g (116 mmol) of [2-(m-dioxan-2-yl)ethyl]triphenylphosphonium bromide are suspended in 160 ml of tetrahydrofuran and treated at -25° within 15 minutes with 77.3 ml (116 mmol) of n-butyllithium solution (about 1.5M in hexane). Thereafter, the mixture is stirred at -25° for 15 minutes. Subsequently, 10 ml of a mixture of tetrahydrofuran and 1,3-dimethyl-3,4,5,6-tetrahydro-2-(1H)-pyrimidinone (1:1) are added, the mixture is stirred at -25° for a further 5 minutes and then treated within 30 minutes at -25° with 20 g (116 mmol) of p-(imidazol-1-yl)-benzaldehyde in 150 ml of tetrahydrofuran/1,3-dimethyl-3,4,5,6-tetrahydro-2-(1H)-pyrimidinone (1:1). After completion of the addition the reaction mixture is warmed to room temperature and stirred at this temperature for 15 minutes. Thereafter, the reaction mixture is poured into 1 l of ice-water and extracted with 600 ml of methylene chloride. The methylene chloride extract is washed with water, dried over magnesium sulphate and evaporated. There are thus obtained 42.2 g of a semi-crystalline product which is dissolved in 600 ml of methanol and hydrogenated exhaustively in the presence of 18 g of palladium-on-carbon (5%). After filtering off the catalyst and evaporation of the filtrate there are obtained 36.6 g of a semi-crystalline residue which, in turn, is dissolved in 700 ml of methanol, treated with 22.4 g of p-toluenesulphonic acid monohydrate and heated to reflux for 2.5 hours. After cooling to room temperature the pH value is adjusted to 7 with 36 g of sodium carbonate, the reaction mixture is evaporated, the residue is poured into 500 ml of water and extracted with 600 ml of methylene chloride. The methylene chloride extract is washed with water and saturated sodium chloride solution, dried over magnesium sulphate and evaporated, whereby there are obtained 36.1 g of a semi-crystalline residue. This is dissolved in 400 ml of tetrahydrofuran, treated with 110 ml of 3N aqueous hydrochloric acid, stirred at room temperature for 3 hours and subsequently concentrated under reduced pressure. Thereafter, the reaction mixture is poured into 500 ml of ice-water and extracted three times with 200 ml of ether each time. The aqueous phase is subsequently adjusted to pH 9 with potassium carbonate and extracted with 600 ml of methylene chloride. The methylene chloride extract is washed with water, dried over potassium carbonate and evaporated. The residue is chromatographed on 240 g of silica gel with methylene chloride and 0-5% isopropanol as the elution agent. There are thus obtained 13.2 g (53%) of 4-[p-(imidazol-1-yl)phenyl]butanal as an oil.
With potassium phosphate; copper(l) iodide In N,N-dimethyl-formamide at 35 - 40℃; for 40h; Inert atmosphere; chemoselective reaction;
94%
With potassium carbonate In dimethyl sulfoxide at 120℃; for 12h; Inert atmosphere;
General procedure for the copper-catalyzedN-arylation of nitrogen-containing heterocycles with aryl halides
General procedure: To a mixture of 0.05 g catalyst and aryl halide (1.0 mmol)in 9.0 cm3 DMSO, Het-NH (1.2 mmol) and K2CO3(2.0 mmol) was added and the mixture was vigorouslystirred at 120 C for the appropriate time under a drynitrogen atmosphere. After completion (as monitored byTLC), the catalyst was filtered, and the filtrate wasextracted with ethyl acetate (3 9 20 cm3) and the combinedorganic layers were dried with anhydrous MgSO4,filtered, and evaporated under reduced pressure. The residuewas purified by column chromatography. The purity ofthe compounds was checked by 1H NMR and yields arebased on aryl bromide. All the products are known and thespectroscopic data (FT-IR and NMR) and melting pointswere consistent with those reported in the literature [36-41].
94%
With potassium carbonate In N,N-dimethyl-formamide at 30℃; for 10h; Inert atmosphere; Irradiation;
93%
With copper(l) chloride; sodium hydroxide; 3-(diphenylphosphino)propionic acid In dimethyl sulfoxide at 120℃; for 14h; Inert atmosphere; Sealed tube;
Copper-catalysed arylation of nitrogen-containing heterocycles with aryl iodides
General procedure: NH-containing heterocycle (1.4 mmol) and DMF (2.0 mL) were added to a mixture of CuCl (15.0 mol%) and ligand 1 (20.0 mol%) in DMF (2.0 mL), aryl iodide (1.0 mmol), NaOH (2.0 mmol). The mixture was vigorously stirred at 120 °C for 14 h under a dry nitrogen atmosphere. After completion of the reaction (as monitored by TLC), H2O was added and the organic layer was extracted with EtOAc, washed with brine and dried over MgSO4. The solution was filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography. The purity of the compounds was checked by 1H NMR and yields are based on aryl iodide. All the products are known and the spectroscopic data (FT-IR and NMR) and melting points were consistent with those reported in the literature.
90 %Chromat.
With C16H12ClN3OPdS; potassium hydroxide In dimethyl sulfoxide at 110℃; for 10h;
2.3. Catalytic arylation of nitrogen-containing heterocycles with aryl halides
General procedure: Arylhalide (1.0 mM), nitrogen-containing heterocycle (1.2 mM), KOH (2 mM), and the catalyst (0.75 M%) were stirred in dimethyl sulfoxide (DMSO) (4 mL) at 110 °C for 10 h. After completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate (10 mL) and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel using hexane/ethyl acetate(70 : 30) as eluent to afford the desired product. The products have been characterized by 1H NMR spectroscopy.
5e) 2-[(4-(imidazol-1-yl)-phenyl]-3-hydroxy-6-acetamido-4H-1-benzopyran-4-one 2-Hydroxy-4-acetamido acetophenone (6 g; 31.06 mmol) was dissolved in ethanol (100 mL), NaOH (6.2 g; 0.15 mol) and 4-imidazoyl benzaldehyde (9.6 g; 55.9 mmol) (prepared according to J. Med. Chem., 1993, 36(20), 2964-72) were then added and the resulting mixture was stirred for 24 hours at r.t. The reaction was diluted with MeOH (100 mL) then H2O2 (15 mL) followed by H2O (15 mL) were added. After 3 hours the yellow solid was filtered, suspended in HCl 3N and stirred for 1 hour at r.t. The precipitate was filtered and dried to give the titled compound as a yellow solid, yield: 77%; 1H-NMR (d6-DMSO): 10.36 (s, 1H); 9.80 (s, 1H); 8.91 (s, 1H); 8.46 (d, 1H); 8.38 (d, 2H); 8.0 (s, 1H); 7.94 (d, 3H) 7.76 (d, 1H); 7.45 (s, 1H); 2.1 (s, 3H); MS (EI) 362 (M+1).
6.3. General procedure for the synthesis of chalcones (3-13 and 16-31)
General procedure: A mixture of azolyl ketone (1a/1b) (1 mmol) and aryloxy benzaldehyde (2a-f) (1 mmol) were dissolved in 10% NaOH-EtOH (5 mL), it was stirred at room temperature for 9-10 h. After completion, 5 mL water was added to the reaction mixture. The separated solid compound was filtered and washed with water. It was purified by crystallization with methanol/chloroform or basic alumina column chromatography to give the desired compounds (3-13).The compounds (16-31) were prepared by the reaction of their corresponding aldehyde and ketone partners.
With potassium hydroxide In methanol; water at 20℃; for 12h;
(E)-5-(4-(1H-imidazol-1-yl)phenyl)-1,1-bis(methylthio) penta-1,4-dien-3-one (6g)
General procedure: To a solution of 1,1-dithiomethyl-1-en-3-butenone (5) (1.62 gm, 10 mmol) in methanol (40 ml), substituted benzaldehydes (4) (10 mmol) were added, followed by aqueous KOH solution (1.12 gm, 20 mmol, in 10 ml of water), the resulting reaction mixture was stirred at room temperature for 12 hr. It was concentrated in vacuo, poured into water (100 ml) and extracted with dichloromethane (50 ml x 3). The combined extract was washed with water (100 ml x 2), brine solution (50 ml x 2), and dried(Na2SO4). The solvent was removed in vacuo and the resulting crude product was column chromatographed (SiO2, 60-120 mesh). Elution with mixture of ethylacetate in hexane furnished compounds 6a-h.
General procedure: B(C6F5)3 (1 mol %) was added to a stirringsolution of aldehyde (1 mmol) in MeOH (6 mL). After 15 min., 5.5 M TBHP indecane (3 mmol) was added slowly and reaction mixture was refluxed untilthe complete conversion of starting material (monitored by TLC). Aftercompletion of reaction, the methanol was evaporated in vacuo. Later, thereaction mixture was diluted with water (20 mL) and extracted with ethylacetate (3 15 mL). The organic layer was washed with cold saturated sodiumbicarbonate solution (2 20 mL) followed by brine. The organic layer wasdried over MgSO4 and concentrated under reduced pressure and products werepurified over silica gel column chromatography in ethyl acetate/hexane. Allcompounds were characterized and confirmed by comparison of their spectraldata and physical properties with reported literature.
1,3-bis[4-(1H-imidazol-1-yl)phenyl]prop-2-en-1-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
76%
With sodium hydroxide In methanol at 20℃;
Synthesis of 1-[4-(1H-imidazol-1-yl)phenyl]-3-phenylprop-2-en-1-ones 4a-o; general procedure
General procedure: A methanolic sodium hydroxide solution (10%; 10.0 mL) was added drop-wise to a mixture of 1-(4-(1H-imidazol-1-yl)phenyl)ethanone(3) (10.0 mmol, 1.86 g), aromatic aldehyde (10.0 mmol) and methanol (50 mL) over a period of 30-40 min with continuous stirring at room temperature until completion of the reaction (as indicated by TLC). The reaction flask was kept in the freezer overnight. The obtained precipitates were filtered off and washed with a cold methanol-water mixture (1:10). Finally the product was purified by column chromatography using CHCl3:MeOH (97:3) as a solvent.
2. To a solution of <strong>[3034-52-4]2-chlorothiazole</strong> (3.8 g, 32 mmol) in dry THF (50 mL) was added n-BuLi (14 mL, 34.9 mmol) dropwise at -78 C under N2. After 1 h a solution of 2 (5 g, 29.1 mmol) was added dropwise at -78 C. The resulting solution was allowed to slowly warm to RT. The reaction was quenched with NFLCl solution and extracted with EA. The combined extracts were concentrated to give a crude oil. The crude product was purified by silica gel chromatography to afford 3 (3.5 g, 41.4 %).
(2R,3R,4S,5R)-2-(2-(2-((E)-4-(1H-imidazole-1-yl)benzylidene)hydrazineyl)-6-amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
81%
In methanol at 80℃; for 0.5h;
General procedure for the synthesis of compounds (12-43).
General procedure: First, 0.5 g of 2-hydrazinoadenosine (11) and different aralkyl or alkylaldehyde compounds (1.1 equivalent) were combined in methanol(30 ml) and heated by microwave at 80 °C for 30 min. The crudeproducts (12-13, 17, 19, 21-32, and 35-39) were precipitated frommethanol, and the other products (14-16, 18, 20, 33-34, and 40-43) were purified from the reaction mixture using silica gel column chromatography. All the crude products were further purified by MPLC on reverse phase C18 material to yield the products(12-43).
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